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I'm an engineer that needs to sell my services. Any good books on sales?
144 points by telecomsteve on Feb 9, 2024 | hide | past | favorite | 80 comments
I recently left my role as a lead devops engineer and would like to work for myself under a devops service contract model (multiple clients, each part-time). Unfortunately, I know nothing about sales or the mechanics of creating and following up on leads. Are there any good books that can explain the tools and workflows of someone who works in sales? Thanks in advance.


Sounds a lot like where I was about twenty years ago, and today I sell stuff for a living... a few thoughts I wish someone had given me...

1) Productize yourself. That is, have several very clear services you offer at established rates. Brand yourself around a very clear idea that has people saying "hey, call the <service> guy" when they need <service>.

2) A lot of us in tech are shy and introverted by nature, which on the surface appears in direct opposition to the skills needed to sell. What I'm telling you is that you can absolutely learn how to be the life of the party - it just takes work and courage, just like any other skill.

3) Sharp branding can make you stand out. Good quality cards, website, etc. Speak well, write well. When you ask someone for a meeting, be very clear in communicating why it is a good use of their time. Figure out early if you are talking to the person with the authority to buy.

4) Small companies will often run you through the wringer of interviews etc, only to not actually have much money. Well-established companies will often be slow to pay and full of bureaucracy, but reliable income.

5) Time-boxing is your friend. It is hard to both do the sales and do the work. You need to really be aware of this as a potential problem.

6) Do sales by not doing sales - there is a lot to be said for meet up groups, speaking opportunities, providing "free" resources, etc. That is - be seen as an expert in your community and people will come to you and/or you will have already passed the social validation test.


Item 1 is key in my mind. As someone in a role that procures a lot of services the worst thing someone trying to get a foot in the door can do is “everything”. Especially if you can’t explain how you work.

It leaves all the burden of figuring out how I could potentially use your services on me, and I’ll try my best to avoid having to deal with that uncertainty on top of what I’m already trying to achieve.

If you want to be successful offering services be very clear about how you work.


I'll second this as well.

Everyone has a "go-to guy". Often it's a plumber, a handiman, a lawyer, etc. Your might be the "devops guy" or the "Cisco guy", etc.

Build that reputation and then expand.

Also, learn to listen well, ask good questions, and take good notes. Communication when you are independent can make or ruin it for you.


> It leaves all the burden of figuring out how I could potentially use your services on me

Thank you for sharing this. I feel a lot of client services businesses starting out (read: individuals going into consulting for themselves for the first time) try to build an enigma to make themselves seem experienced and comprehensive. As a buyer, I want to know, up front, what exactly an engagement with you looks like: What will you do? How much will it cost, over what schedule/criteria? What does our feedback loop look like as we progress?

If I get the impression that you're so desperate for work, you'd agree to do anything and everything for money, I'll feel uneasy. If you're confident about being able to do [thing] well, and can explain what it looks like for us to do [thing] together, it will put me more at ease.


#1 is something I have a hard time with. I'm a developer who became a generalist and my specialty is not one particular thing. The corporate world wants to pigeon hole me into being a product manager, I'm only average at that. Being able to blend engineering, product, some marketing and general leadership skills is my thing. I can kind of do everything, but I don't know how to make a clear list of services to explain. myself. The contracts I've done so far I've stumbled into and only been successful because of my blend of abilities.


Rather than specializing in a skill you could specialize in a market or domain e.g. digital services for furniture manufacturers (probably not a domain you personally are familiar with, but just an example).


So far I've been finding myself bringing product marketing to companies that don't already do it (they bring me in to improve engagement and product marketing is the low hanging fruit). I really don't want to get pigeon holed into that though.


What about branding yourself as an "Engagement Consultant"? That's a more defined service with plenty of demand (probably) and doesn't quite pigeon hole you into one type of activity.


Consulting!!


Sounds like who you're targeting right? Big corps don't need generalists, start ups do.


#2 is particularly insightful. I’m an engineer who strongly dislikes social dynamics, so this point resonates with me.


I have a lisp, a stutter, and would be happy to live in a cabin in the woods far far away from civilization... but I got out of tech and now make a living in real estate and I'm active in politics. If I can learn the techniques to play an extrovert on TV, then anyone can do it. You have to have a plan for how to develop the skills and you have to put work into it, but it really is possible for anyone.


Would you mind if I reached out to you? I have the same stuff, but I haven’t been able to find any good coaching or books on speech.


I will email you, but really I don’t know that I can be much help. I did speech lessons as a really little kid, but don’t think they helped much with the lisp. The stutter comes and goes - I will suddenly have a run where it’s happening a lot and then it goes away. Not sure if it is tied to stress or sleep or ?? Started very young but has never been so pronounced that I’ve sought to do anything about it - I generally don’t even think about it, but lately it’s been back again.


https://www.amazon.com/Secrets-Consulting-Giving-Getting-Suc...

The Secrets of Consulting: A Guide to Giving and Getting Advice Successfully by Gerald Weinberg


Seconded. All books by Gabriel Weinberg.

Some books you read to reflect upon or be better informed. His books instead, are likely to change the way you conduct your business, or validate correct behaviors you adopted instinctively.


Damn auto-correct. Of course it's Gerald Weinberg. I have my favorite: "Are Your Lights On?: How to Figure Out What the Problem Really is" just on my table right now :-)

Can't edit my comment anymore, so leave the correction here.


Highly appreciated book. But the author is Gerald Weinberg.


True dat, corrected my mistake. A great author indeed.


Optimising for sales at the beginning is just not worth the time.

You have to start with word of mouth to test out whether your offering is really going to work, with kindly/friendly people who already know you as a person and aren't going to panic and get demanding in a way that a customer can do with someone they don't know from Eve.

And you'll need to be earning enough to at least partly offset the raid on your savings to give you time to think through sales strategies.

Freelance devops is often _not_ fun though; your biggest challenge will be controlling the seemingly unbillable work that you end up doing where people really only want to phone you up and get advice. Goodwill kills, so set boundaries with your early clients.

So if you are wise you will have a consultancy package that you can use to control that. And you'll have some sort of pre-paid token/bucket/time allocation system that encourages your clients to use your time wisely for the small stuff, so you can concentrate on the bigger stuff.

(When I say “if you are wise” I don’t mean to patronise. I mean “don’t just pretend it’ll be OK like I did”.)

Further thoughts (learned the hard way)

Consider how your off-ramps are going to work. Clients who are dependent on you but always make the cheap/expedient choices can become a millstone: they have to take your advice or you will end up resentful.

And consider how you are going to manage price rises.


"And you'll need to be earning enough to at least partly offset the raid on your savings to give you time to think through sales strategies."

This has been my strategy so far. I got laid off 9 months ago and I've barely touched my severance, but I'm also making way less than before and not really saving any money. Could be worse I suppose.


The major lesson will be to ask for the sale. And work that into the conversation, so less "that'll be $99", but more like "So, would you like the blue or pink one?"

If you don't ask for the sale, you won't get it. If you're solving a problem, making the sale is helping people. They came to you for help for a reason, so treat them well.


This x 1000.

"No askie, no gettie" is something my co-founder and I say.

I'm the engineering side and struggle with it, but he's really good at it.


Yes, you should ask for the sale. But "So, would you like the blue or pink one?" might come across as a bit pushy. "would you like to discuss pricing?" is more of a soft close.


There's a subtle difference there - the first is asking "past the close" but also is asking a pertinent question about it - people who want it will have a color they want, or need to pick one.

Nobody wants to discuss pricing. It's orthogonal to getting the desired end. You have to discuss pricing, but it is not on the list of things people want to do (if you give it to them free, they won't protest). The second is way too easy to say no to.


Some of this may also be cultural. Something that works fine in the US, might be seen as pushy in the UK, for example.


It’s pushy here, too.

I think the difference is willingness to be pushy if that pushiness results in more total sales. Which I take as a symtom of general lower consideration for others, objectifying them as a system you just need to press the right buttons on to get what you want.

[edit] Another way of looking at it is what a culture considers acceptable freely-given consent. If someone wouldn’t have said yes if you hadn’t pulled out every trick in the book, is that an OK way to get a “yes”? In US business culture, it is.


I think it might seem pushy to people that are highly skeptical of the product, but in most cases, a sale is implied. When you go to Starbucks, they ask what they can make for you. They don't say "Let me know if you want to talk price."

Car sales is another obvious example. They don't talk price until you're committed (at least in principal) to purchasing the car.


> "would you like to discuss pricing?"

Nobody likes to discuss pricing!

Early on in the call, tell them your price to see if they object. If they do, then get off the call. If there's objections, raise them early and either overcome them or figure out that they can't be overcome.


Less of a problem than not having sales


I've had great success with Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress

"For a lot of us, selling feels icky. Our stomachs tighten at the thought of reciting features and benefits, or pressuring customers into purchasing. It's really not our fault. We weren't taught how to sell, plus we've been sold before, leaving us with a bitter taste.

Here's the truth: sales does not have to feel icky for you or your customers. In fact, with the right approach, sales can be an empowering experience for all.

Bob Moesta, lifelong innovator and coarchitect of the "Jobs to be Done" theory, shares his approach for flipping the lens on sales. Bob shifts the focus of sales from selling, to helping people buy and make progress in their lives--demand-side sales.

Now, in Demand-Side Sales 101, you'll learn to really see what your customers see, hear what they hear, and understand what they mean. You'll not only be a more effective and innovative salesperson--you'll want to help people make progress."

https://www.amazon.com/Demand-Side-Sales-101-Customers-Progr...


I am an engineer and have been working in Sales Engineering for more than 15 years now. You are on an interesting and fruitful quest and I wish you well.

The biggest shift in moving from engineering to sales is that your priority is no longer being the smartest person in the room. Unless, of course, you understand that the smartest person in the room is the person who gets the deal done in a mutually advantageous way. There will always be someone who wants to appear smarter than you, LET THEM. Your goal is to make a living.

The one thing I would say to remember is that your integrity is the most valuable thing that you have, bar none. Don't trade it away for anything. Over the long-term, sales is about finding a great solution that meets the needs of your customer, not winning deals or negotiations.

Here are a few books I found useful in my journey: * Let's get real or let's not play - https://www.amazon.com/Lets-Get-Real-Not-Play/dp/1596592060 * The Three value conversations - https://www.amazon.com/Three-Value-Conversations-Customer-Lo... * Never Split the Difference - https://www.amazon.com/Never-Split-Difference-Negotiating-De... * Leadership is Language - https://www.amazon.com/Leadership-Language-Changes-Differenc... * Draw to win - https://www.amazon.com/Draw-Win-Course-Innovate-Visual-ebook...


I recommend Jonathan Stark's writing on this: https://jonathanstark.com/

His daily email list gives me regular reminders of how to improve in sales and pricing.

His books are brilliant too. Start with Hourly Billing is Nuts: https://jonathanstark.com/hbin


Couldn't agree more. Also look into Alan Weiss's books. Avoiding the hourly billing trap via fixed fee pricing (preferably with value-based pricing) will the best decision you make both for your quality of life and wallet.


Sorry I know this is a relatively late comment, but I recently did a summary on Sam Altman's recommended reading list and I had a great time reading 'How I Raised Myself From Failure to Success In Selling (by Frank Bettger).' I actually provided a full book summary near this end of the post: https://photonlines.substack.com/p/sam-altmans-startup-advic...


Don't worry too much about tools to start. The most important thing is starting, getting consistent, and having a GTM strategy. (Don't overlook the last one.)

  * Be consistent in your outreach
  * Shortcuts like automation are a waste of time unless you're replicating success
  * Always ask for the sale
  * All meetings should have a next step / action. Preferably chain meetings together so you have the next one scheduled by end of current one.
  * "SOGOTP" - you need to respectfully but quickly move conversations to *sales* convos. If someone isn't going to buy, recognize it quickly and move them to nurture instead of taking your time
I'm not an expert here, but I completely failed for 18months w/ 0 customers. Versus current startup where my co-founder is actually good at sales and we're at 1.5M ARR in a year. So I've seen both sides of the coin.


Being aware of the Pareto principle may help guide future decisions. You will find it applies to most facets of life, including Sales and Costs. https://en.wikipedia.org/wiki/Pareto_principle


Hey Steve, I don't have a book recommendation but rather some short advice.

  - Don't expect your client to understand the work you do the way you understand it.

  - A corollary is that you cannot expect the client to put the same price on your work as you would or want.

  - Another corollary is that you will inevitably lose some bids.

  - Value-based pricing has been way simpler to deal with for me.

  - Hourly pay only for a retainer or a fixed amount of hours per month ("I'll be there when you call."). Otherwise I find that incentives get misaligned.

  - Requirements and client desires can change every single time you speak to them, so communicate often. I've been lucky with inflating time estimates by 25-33% to account for this inevitability.


Founding Sales is a tad out-dated but would still recommend to any founder starting a Startup. You can read it for free online or buy a copy.

https://www.foundingsales.com


I liked Founding Sales a lot, and, re-reading one chapter today, I still do. In what way do you see it as outdated?


I know you're looking for a book recommendation (my recommendation would perhaps be a bit too socializing-weighted with Never Eat Alone by Keith Ferrazzi) — but I also wanted to reiterate what others have said here already. It's a two-step process — you need to get in front of a potential client, and then you need to convert them into a sale (project). I personally think that most books focus on the latter, whereas the former is arguably the hardest part: finding leads.

It's the same problem most indie devs and startups have (without VC-infused Adwords budgets) — getting their product in front of other people.

I have been consulting in a self-employed capacity for 13 years now, next to doing other things, and 100% of my leads have come through friends, exclusively. This is not to show how great my friends are (debatable), but how I have been completely unable to attract business outside of my network, even in 13 years!

Marketing yourself to even be considered a point of contact for whatever it is you're offering is - in my opinion — by far, the hardest nut to crack.

I'd love to hear suggestions by others who've been successful on this front, especially how you attract out-of-network leads. It seems next to impossible at times, except for those rare (serendipitous) moments when someone reaches out after a newspaper article or being featured online somewhere.


SPIN Selling by Neil Rackham[1]

This site give a good preview/summary of the book/method: https://blog.hubspot.com/sales/spin-selling-the-ultimate-gui...

[1]: https://www.amazon.com/SPIN-Selling-Neil-Rackham/dp/00705111...


A couple of strategies:

1. Find a recruiter who will work for you to place you in a 1099. Maybe pay them a commission for the lead or a successful placement.

2. See if a larger consulting company will subcontract to you.

3. Look for devops jobs in your network and see if they'd be open to a contractor.

3. Look for city/state/federal RFP opportunites recently funded or to be funded. Then go to step2


The only thing that really works is contacting someone in your network(ex-work colleagues, ex boss, college friends and so on).


Public speaking engagements and conferences are other ways to grow that network.


You should read about Nick Disabato at https://draft.nu/about/

This is the one service and its website that I keep recommending to people asking for how to establish their services for a specific niche and be extremely good at it.


Fanatical Prospecting and Objections by Jeb Blount.

These are very full-time-sales-oriented books, and they may be too much for what you need. That said, they might be spot on.

In general, I would:

1. Talk to your network. This will yield your warmest leads.

2. Find a niche of clients who really have a tough time finding people for whatever reason. A good example for tech might be small town governments — they have needs and money, but they don’t have knowledge/expertise or funds to hire a lot of full timers. Target those groups and/or find out what contractors work with those groups and sub with them.

3. (Related to above) Find a bigger agency and just subcontract out with them. This might be a little lean in terms of money at first, but it will introduce you to a specific industry space both in terms of problems and people who solve them.

Good luck!


This might sound obvious, but it’s often conflated - make sure you understand what exact business you’re in.

Eg, you say you’re an “engineer” but it sounds like you want to sell a consulting service. Make sure you align your messaging to match what you’re exactly selling. Because many might confuse hearing “engineer” with you starting a product company.

Also, if you’re in the consulting business - make sure you understand what it means to be an independent consultant. Because cash flow, lead gen, etc are all real unexpected challenges for folks in this specific business.

Then, what kind of liability do you need to be a consultant. Are you going to bill based on an hourly rate or fixed fee. Are you doing pure staff aug, or something else.

Again, it all come down to understanding what exact business you’re in.


It's not that hard. Afterall, salespeople can do it. ;0)

I have to be salesman for my own software sometimes. The approach varies with the market and proce level. But basically:

-be personable and professional

-take the time to understand their needs

-if you think you have something that fits their needs, ask for the sale ("would you like to discuss pricing?")

-follow up periodically until they buy or you decide they aren't interested

-don't try and sell something that is a bad fit

-develop a thicker skin

You don’t have to be dishonest or pushy.

Useful guideline:

- 1:many is marketing - 1:1 is sales

See also: https://successfulsoftware.net/2018/03/21/tracking-your-sale...


Winning through intimidation https://www.amazon.com/Winning-Through-Intimidation-Robert-R...


I'm assuming folks downvoted this to dead because they judged the book by the cover! This is a really good book and not "as dark" as the title seems at first. I highly recommend this book. It's an intriguing and easy read.


https://www.winwithoutpitching.com/books/

https://fanaticalprospecting.com

https://storybrand.com

I've liked all of those books.

Biggest takeaway is that you'll be worst off if you try to figure out how to sell well. Just start selling.

If you have a target market and a product to sell, pick up the phone and start dialing. Get a LinkedIn Sales Navigator Account and start doing outreach.

You're not going to get good at sales by any way other than trying and failing.


The best books I found when I was doing exactly this were the books by Harry Beckwith, starting with "Selling the Invisible". He focuses on services sales, and how you create a perception of value for your service.


To Sell is Human by Daniel Pink is a great book for integrating sales into your mindset by realizing how much of it you already do on a day to day basis. As a consultant engineer it's completely changing my mindset.


Over 30 years ago I found myself in a similar situation. I took a Dale Carnegie sales training course to learn selling techniques. I was the only one in the room with no "product" to sell. The simple techniques have been one of the most valuable skill I have learned in my career. Go get the Dale Carnegie books. They are on Amazon, they are inexpensive, and they are timeless. Good Luck.


Although learning new skills is fine, I think your question is hinting at a deeper problem: it's difficult to acquire customers in this field. Presenting that problem as "I need to learn about sales" may be to misunderstand the problem. It's possible that (for <reasons>) there is no decent market to sell part time ops services and no amount of sales chops will solve that problem.


I don't think there's 1 single book on selling that is goo, your best best is to always keep on reading.

I would incorporate:

* Never Split the Difference

* So Good They Can't Ignore You

* This is Marketing


Related: https://hackertimes.com/item?id=33224240


New Sales. Simplified.: The Essential Handbook for Prospecting and New Business Development by Mike Weinberg

Chapter 14: planning and executing the attack, is brilliant!

Feel free to DM, if you want to compare notes

> https://www.goodreads.com/en/book/show/15863998


Looks like you've just taken the first step. TopTal is possibly a good service to get your name out there.

I'm currently in search of a full-stack engineer to work on a project part-time. If you're interested in hearing more let me know.


Five things they don't tell you about economics https://img.pr0gramm.com/2017/06/15/ac3de81044c3a9a6.jpg


Not your question, but the National Labs are hiring https://nationallabs.org/work-here/careers/


Prospecting Your Way to Sales Success, by Bill Good.

Although mostly about telemarketing, it's mathematical point of view is unique and will delight your engineer brain. It's principles are still used extensively in financial services.

Made me a bunch of money.


I recommend "to sell is human" by Daniel Pink to anyone unease about starting basic commercial interaction. I have received good feedback so far from those I recommended it to...


"The Trusted Advisor" by David Maister. (It's more about what makes you sellable than sales. And it's more than being a great engineer that makes you sellable.)


Ive enjoyed the classical sales books like SPIN selling, Challenger sale, Fanatical prospecting, The Psychology of Selling.


for Stream I took the first 200 sales calls myself. I think you need to really just go do it a lottttt. Ignore all the books, just focus on understanding the customer's pain point and follow up faster and more often than any big company would.


Less technical but you might find Proximity principle by Ken Coleman to be helpful as well.


Growth Hacking by Ryan Holiday

Alex Hormozi's 2 books

- $100M Offers

- $100m Leads


Value-based fees by Alan Weiss


I like and recommend this one, but I also think he pulls a lot of sleight-of-hand... a lot of it is based on the premise that the client is willing to share (or can even get, in big enough companies...) numbers that inform the value created. For a tech consultant bopping between companies and industries, it's really challenging to come up with these numbers. Likewise, I found that even if you can prove a number, getting a big company to bite on it (unless you are truly talking to a Cx0) is nearly impossible... case in point... a major west-coast health care company had a crisis. I found the problem and laid out a path for a few million dollars to solve the problem. It was somehow way easier to pay IBM $50MM to "solve" the problem rather than the $10MM or less by actually fixing the problem. You run into a lot of that at the Fortune 500, which makes it clear it isn't about "value". Weiss seems to gloss over a lot of this.


You probably weren't talking to an economic buyer.


I was and I wasn't - and in fact we knew we didn't really have a shot at getting to the economic buyer who made the choice to spend stupid money. But that's kinda my point - most of us are talking to mid-level management and down when we are interacting as solo operators / small consultancies into larger clients. That Director you are interacting with likely doesn't have the authority to authorize anything beyond a consulting contract at $xxx /hour as they are going to have someone in finance scrutinizing their spend.


Million-Dollar Consulting is as good or better


I'd agree with this - Weiss covers really everything he has to say in this book and many of his other books like Value Based feel like a way for him to capture additional book sales as much as having something new to say.


Id recommend just giving it a shot and not reading books about it. You'll learn way more, way faster. And it'll be hard, there will be constant rejection, and there will be mistakes, but it's the only way. Speak to people, message people, put yourself out there online and in person. Follow up when people may be interested, and don't follow up if people arent. All you need is a contract / statement of work / agreement if your havent already, and get a business to sign it. That's all there is, everything else is a distraction. Forget every other theory about sales, it's certainly not a science but there's a world of snake oil sales people - selling to sales people - it's nearly all bullshit. Just know what your offer is and see who wants it. Youre no doubt a smart and capable person if you're a lead DevOps I'm sure, you will get hired and paid, confidence and applied effort is all you need. Good luck. I say all this confidenently as I sell software services for a living, I'm good at it (with all humility).


Influence The Psychology of Persuasion by Robert B Cialdini.


Very good advice for consultants and freelancers: https://www.youtube.com/watch?v=jVkLVRt6c1U

TL;DR: Make good consulting contracts with a proper lawyer


I am in the same boat and am interested in the same type of books!

If you'd like to have some accountability and some sort of light book club kind of thing let me know, as well. I am a social creature and would love to collaborate.

Also, I have reached out to a SaaS sales guy I know for some personal coaching... happy to let you know how that goes after this weekend :)

My partial reading list while I wrap up at $dayJob:

- Corporate Rebels

- Secrets of Productive People

- Docs for Developers

- Influence, new and expanded (kinda meh so far)

- Cult of the customer

- 48 Laws of power (kinda gross, honestly)

Finished books I would gladly re-read

- Disruption

- Peopleware

- Never split the difference

- The Scout Mindset

- How to win friends and influence people

- Amusing ourselves to death


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